#5 CM Punk - 2009 - 2010
As documented recently of the WWE Network's 'Something Else To Wrestle With Bruce Prichard', CM Punk's early push in WWE was full of stops an false starts, as some higher ups saw a star in him, while others didn't.
After his for WWE World Heavyweight Championship reign came to a premature end in 2008, Punk received an unexpected shot right back up the ladder in 2009 when he won his second Money in The Bank contract and World Heavyweight Championship. During this run, he became WWE and wrestling's next best heel.
A top AEW star just called one of his colleagues 'spoiled' and 'narcissistic' HERE.
He had an excellent feud with Jeff Hardy over the big gold belt, and then moved onto The Undertaker. Fans were anticipating a Match of The Year like performance from these two at the Hell in A Cell event in their World title Cell match, but instead the Taker easily defeated Punk for the gold in less than 10 minutes. Punk got one multi-man rematch a few weeks later, then went right back down the card.
Punk later spoke on this, claiming he had upset both The Undertaker and WWE management by not taking Taker's advice to dress more sharply as Champion in public. Punk said he complained to management that he should be able to wear his t-shirt and jeans punk rock style look, since then WWE Champion John Cena was allowed to wear his hip-hop attire during his public appearances.
As everyone knows, Punk finally regained his push and went strait to the top in 2011.